We kind of love this. The shoes take it straight to “Colorful elderly New York City heiress” territory.

Maggie Gyllenhaal out and about New York City.

Everything else is high end until you get to the footwear, which looks like something she bought off a spinner rack at a Duane Reade. It’s the hat that really gives it that insouciant “Lovey Howell on a bender” feel to it.

Man, we are NEVER going to be invited to the Saarsgaard/Gyllenhaal’s for dinner and drinks, are we? Daammit.

They are leather Isabel Marant and retail around $500. Sad, but high-end.

Plus, they fit right in the trend of Birkenstock becoming a fashion shoe. Or that’s maybe just European fashion and Maggie is joining the EU fashion wagon!

Constant Reader

I remember when Birkenstocks had a brief moment as a fashion shoe in the 90s. I wish I didn’t.

Karen Belgrad

Do you think the sandals are her equivalent of the “Working Girl” sneakers? Are her fancy pumps in the bag?

http://www.youtube.com/user/TheOctocornNetwork International Model

Maybe she’s heading to that river Carly Simon kept singing about…

Noah

“Lovey Howell on a bender.”

Now THAT I want to see.

http://www.youtube.com/user/TheOctocornNetwork International Model

I think you can – Youtube Elaine Stritch’s “Ladies Who Lunch”.

MartyBellerMask

RIP

http://www.youtube.com/user/TheOctocornNetwork International Model

I want Instagram justice – I did this look with a red hat five months ago (with fishnets).

Constant Reader

I really, really want to hang out with you. Alas, I’m pretty sure we are on opposite coasts.

http://www.youtube.com/user/TheOctocornNetwork International Model

This is one of the nicest things anyone has ever said to me. And this is America – where reasons to travel are plentiful. Bitter Kitten meet ups are inevitable.

Skippymom1

I practically wept when we got to her Kmart feet. The rest of the look is so lovely.

Sarah

That hat is badass. Why does she eschew brassieres? What up with that.

nannypoo

She has a really cute little body. I would be willing to bet she is also not wearing underpants.

Sarah

Heck yeah. Screw that jazz. Commando FTW.

myandyleigh

I covet the dress, and maybe even the hat. She can keep the shoes, though. Please, keep the shoes.

FibonacciSequins

I fully sympathize with the need for comfortable summer walking shoes in NYC, but she can do better.

hughman

OMG. These pics literally made me LOL. This is the best. She is just full-on “I HAVE NO FUCKS TO GIVE”.

StellaZafella

I really love ‘er…and, as of this post, I will officially dub her (for my own purposes only): “Mad Aunt Maggie”

MartyBellerMask

Those sandals are a double middle finger to Taylor Swift.

FuhUgh

And I LOVE the statement!

FuhUgh

There may actually be some things IN that purse. After various parking lot tours this summer, how refreshing. She is actually dressed to go somewhere and do something and say “screw off” to the rest of you.

EveEve

She has half a leftover falafel pita in that bag, along with her kids’ almost-empty organic sun screen, the macrame keychain with the evil eye beads she picked up in Istanbul, her Ipod, an overdue water bill, and her frequent flyer coffee punch card from Milk & Roses in Greenpoint (just kidding on that last one – they don’t do punch cards). Oh, and her personal vaporizer. That’s the way she rolls.

LadyVimes

Love the hat though.

Lauren Frankel

“Daammit” LOL

MilaXX

I kinda love it. It’s like some stylist gave her a cleaned up version of her natural style.

Gatto Nero

1,000 points for the Lovey Howell reference.
Made my day.

Imasewsure

“Lovey Howell on a bender”… Yes!! Love the dress though…

And maybe she gave her real shoes away to some needy person outside Duane Read? Let’s go with that…

carrie

I think we need to talk about ugly sandals and their hopefully short resurgence in fashion. Birkenstocks, I’m looking at you and blame you for the above as well.

MartyBellerMask

I prefer it to hooves or spikes or jelly or whatever misogynist contraption that passes for shoes these days. Comfort is a trend I can live with. Maybe that’s just me; I like Birkenstocks. Crocs, no. Birks, yes.

carrie

I love comfort too! But comfortable can be cute. I cannot stand the Birks. They are not chic or fashion.

vitaminC

Oddly enough, Birks have some really cute fashion-forward styles now. I was shocked.

carrie

No!

enchanted216

She looks great for 70.

mickiemonkey

Those shoes say, “I ran out of Klonopin”.

nannypoo

I love everything about this, even the awful sandals. She looks comfortable and sort of coordinated, for her, and I’m guessing she does not care what we think anyway.

Glam Dixie

Those sandals are something my 60 something mom would wear. Btw, what is Duane Reade? I used to go around when I was a kid talking with my teeth clenched, I do a killer Thurston Howell impersonation.

FibonacciSequins

It’s a drugstore chain (currently owned by Walgreens) in New York, named after the two streets in downtown Manhattan where the first store was located.

Glam Dixie

Ah, thank you. I figured it must be something exclusive to the area.

Tammy_4

Damn it, I turn 60 tomorrow. And I would wear those sandals. And that dress.

Glam Dixie

That dress is cute and the sandals are ok, my mom has pretty good taste. Happy birthday!

Grumpy Girl

Thank you for asking!

ashtangajunkie

This is a joyful combination of fantastic and hilarious.

Sherilyne Cox

I’ve seen better looking slaps leaving my nail salon.

JauntyJohn

That hat is EVERYTHING.
While everyone can put a hat on their head, not everyone can “wear” a hat.
This woman schools us all.
Footwear shmootwear, she is giving me Lovey Howell LIFE.

ShaoLinKitten

Wow, I think my dad has those same sandals. He is an 82 year old Jewish man who wears them with blindingly white tube socks.

BayTampaBay

Does he live in Florida??? You see a lot of sandals with white tube socks down here.

Lilah

Funny. Those are super expensive Isabel Marant sandals.

http://viridianpostcard.blogspot.com/ viridian61

The Holden, for $510 at Barney’s.

Laylalola

See, this is why labels mean shit. She’d look 100 percent more fashionable in a $25 pair from Old Navy.

Dan_In_NYC

This look is 100% perfect for what it is. Nice work Gyllenhaal.

SewingSiren

I think she went into the Duane Reade because she got an unexpected vist from Aunt Flo. She isn’t in the mood for any picture taking.

@Biting Panda

Living for this.

Tigerfly

I’m hoping that the cute but less comfortable sandals are in her bag…

Sally Shield Mabadi

I think those sandals are Isabel Marant.

J.W.

Could be…or some other high end designer cashing in on the dorky shoe trend…and there are plenty of them.

http://pulse.yahoo.com/_QFW22QV426LUOEPGASPZJWJMDE MishaFoomin

Her purse is on the wrong side. How am I supposed to judge its fullness??

bitchybitchybitchy

Love the hat, the dress, the sandals? Not.

OffToSeeHim

Hate it, hate her, big OUT.

Mothra

Is that what one would call “resting bitch face?”

P M

I would have joined the hating, but I know how hard it is to find comfortable footwear that don’t look like two wedges of cork on one’s feet! The hat could have been changed, though.

livesarah

I think I should hang out with Maggie. I like to wear high-end dresses with flip-flops too. It probably doesn’t look great, but who needs to look as dressed up as Taylor Swift just to go shopping? Comfy footwear FTW.

quiltrx

Those are “going to the mailbox” shoes, darling. Nothing else.

crash1212

I’m loving this. I don’t even hate the footwear because I know they cost a fortune and are very comfy. I forgive less fashionable footwear on a hot summer day. Let Maggie live.

http://www.ellenciompi.com/ NurseEllen

“Lovey Howell on a bender”—THAT, ladies and gents, is why I will always sing the praises of TLo. Spot. On. Perfection.

mercer bleecker

Those are Isabel Marant Holden sandals. I love them!

Violentcello

Heavens to Betsy, I love that hat. It looks fantastic on her.

GillianHolroyd

Agree, that hat is Garboesque.

Pepper Collins

Those sandals can’t be real. They look like they’ve been photoshopped in!

nannypoo

I checked out the sandals. They cost $510 at Barney’s. They’re still ugly, but at least they’re sort of high-end compared to crocs or birks or some of the other footwear that they might remind us of. And her dress and hat and attitude are worth way more than $510, so I still love this look. Anyway, as I type this I am wearing my favorite pair of Birkenstocks, so I am not really in a position to criticize her footwear choice. I think she’s sort of adorable.

PastryGoddess

Birkenstocks are much more attractive than those shoes.

THOSE SHOES COST $510!!! I’m obviously in the wrong line of business

AndieJay

How did the photog even know that was Maggie? I guess it’s their job, but wow.

Tracy_Flick

Girl, I get it. I feel like a busted can of biscuits some days too.

http://twitter.com/#!/Space_Kitty Space Kitty

Five. hundred. and. ten. dollars.

I have the exact same pair in my yoga bag for wearing out of the shower. $10 at CVS and I was ashamed to have overpaid.

Judih1

Yes TLO is NEVER going to be invited to the Gyllenhaal household. Your fate was sealed when you referenced “nursing home pee” on one of her outfits a few years back. A classic line!

evave2

On the thumbnail I only saw her to just below the waist. I thought, she looks nice. I actually like the hat (my husband would say it keeps the sun off her face and lessens her cancer chances; he talks about this a LOT to me, says I need to wear a hat.) THEN WE GOT TO THE SHOES. WHERE IS SHE GOING? I can only think it’s to the zoo for a 3-mile hike with misbehaving children in tow. These are not good shoes. They look like shoes where you have to grip with your toes (not like Nina Dobrev’s clenched tootsies but the same result) and the PAIN is going to be painful.

BayTampaBay

Actually Nina Dobrev has a severe case of “Hammer Toe”. Hammer Toe is very common and tends to be familial.

demidaemon

It’s a little nightgowny for me. Sorry. Love the hat, though.

Snailstsichr

I bet it would look less nightgown-y if she was wearing a bra.

demidaemon

Perhaps. The print and shape aren’t helping. Neither are the shoes.

MartyBellerMask

Cute earrings.

Alyssa_T_Robot

i want her to wear that hat and sunglasses ALL THE TIME.

SugarSnap108

I don’t know see why you would be invited over for dinner, TLo. I think she’d dig everything you wrote about this look.

Chickadeep

“Lovey Howell on a bender”—PERFECT!! This is the fashion ethos I will be aiming for when I hit my 70s.

Shawn EH

Maggie’s getting a head start.

MarandaGodbolteam

I just >­OPEN NEXT TAB FOR MORE INFO AND HELP

3boysful

OK, now the Saarsgaard/Gyllenhaals simply must invite you buys to dine, just to show they have a sense of humor. (And they could return some vowels for the rest of the words to use, too.)

Betsy

That dress is beautiful. I’d be tempted to tear it apart and make throw pillows.

Dorothy & Michael n/a

Is anyone watching her new mini series on Sundance? “An Honorable Woman” premiered last week, and the second ep is on tomorrow at 10 PM. It’s really, really good and previews look extremely promising. It’s gotten very positive reviews, too.

And the sandals? They might be expensive and comfortable but they’re still pretty ugly.

msdamselfly

The hat color doesnt go with the dress

NinjaCate

She’s embracing her inner Margolit!

http://phantomminuet.blogspot.com/ MinAgain

Oh, Maggie. Never change.

MandyM

I kind of love this. I love her!

Radish

You’d think for $510, you could get some comfy shoes that aren’t fugly.

Kathie

The dress is fab. The hat doesn’t go with the dress and well we all know how we feel about the shoes. Lose the hat and put on a different cuter flat sandal and we’re in business.

http://victoriapavlova.com Victoria Pavlova

Her head belongs to someone much more stylish than what is going on below her neck